Chiral cyclobutane synthesis by exploiting a heteroatom-directed conjugate addition

Organic Letters

Volumn 12, Issue 22, 2010, Pages 5338-5341

  Tsao, Kuo Wei ^a   Isobe, Minoru ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE; EPOXIDE; LEWIS ACID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLOBUTANES; EPOXY COMPOUNDS; LEWIS ACIDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 78449292890     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102383g     Document Type: Article

References (25)

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23. In this case, the syn -isomer is defined as the same face of the incoming methyl group and neighboring oxygen atom, when drawn in zig-zag main carbon chain according to S. Masamune's definition.
24. This may have stereospecifically happened, after the cyclobutane formation, to one of the diastereomers, which posessed the stereochemistry orienting the sulfonyl group trans to the propargylic proton. An excess carbanion attacked the propargylic proton and eliminated the trans -sulfonyl group to give cyclobutene 14.
25. The ORTEPs of cyclobutene 14b and the p -nitrobenzoate derivative of ent -15a are also included in the Supporting Information.